Diethyl Pyrocarbonate → N-[[2,6-bis[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]-2-[(4-chlorophenyl)sulfonyl-ethyl-amino]prop-2-enamide

HRID 1479837ノート

反応式

HRID 1479837 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:17][CH3:18])[C:12](=[CH2:16])[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[F:30][C:31]([F:57])([F:56])[C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[C:42]([CH2:44][NH2:45])[CH:41]=[C:40]([C:46]3[CH:51]=[CH:50][C:49]([C:52]([F:55])([F:54])[F:53])=[CH:48][CH:47]=3)[N:39]=2)=[CH:34][CH:33]=1>C1COCC1>[F:57][C:31]([F:30])([F:56])[C:32]1[CH:33]=[CH:34][C:35]([C:38]2[CH:43]=[C:42]([CH2:44][NH:45][C:13](=[O:15])[C:12]([N:11]([S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])[CH2:17][CH3:18])=[CH2:16])[CH:41]=[C:40]([C:46]3[CH:51]=[CH:50][C:49]([C:52]([F:55])([F:53])[F:54])=[CH:48][CH:47]=3)[N:39]=2)=[CH:36][CH:37]=1

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 90384398[2,6-Bis[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamineHCID 1317365862-[(4-Chlorophenyl)sulfonyl-ethyl-amino]prop-2-enoic acid

生成物 1

HCID 90384162N-[[2,6-bis[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]-2-[(4-chlorophenyl)sulfonyl-ethyl-amino]prop-2-enamide収率 21%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Acid 4D (289.74 mg, 1 mmol) was dissolved in 10 ml of THF and at rt DEPC (1.1 equiv, 0.15 ml) and [2,6-bis[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 29A (1.1 equiv., 400 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (3:7 EtOAc:petroleum ether) afforded 140 mg of a white solid. Yield=21% 1HNMR (DMSO, 400 MHz) δ 1.25 (3H, t), 3.40 (2H, q), 4.60 (2H, d), 5.18 (1H, s), 6.18 (1H, s), 7.70 (2H, d), 7.82 (2H, d), 7.86 (4H, d), 8.02 (2H, s), 8.40 (4H, d), 8.89 (1H, bt) [M+1] 668.9 (C31H24ClF6N3O3S requires 668.05).

後処理

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionThe residue was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude by chromatographic column (3:7 EtOAc:petroleum ether)

出典と根拠

ORDレコード
ord-16b63bb9faef4defa55876e3264acd4b
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

反応ノート

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